Sodium hydride → HCID 58687972, compound

HRID 132849Notes

Reaction equation

HRID 132849 reaction equation
[Br:1][C:2]1[C:3]([O:15][CH3:16])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([Br:10])[C:7]=1[CH2:8][OH:9].[H-].[Na+].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>O1CCCC1>[Si:19]([O:9][CH2:8][C:7]1[C:6]([Br:10])=[C:5]([C:11]([F:14])([F:13])[F:12])[N:4]=[C:3]([O:15][CH3:16])[C:2]=1[Br:1])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 58687965HCID 58687965, compound

Product 1

HCID 58687972HCID 58687972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound from Step D above (880 mg, 2.41 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (60 weight % dispersion in oil; 107 mg, 2.65 mmol). After 30 min at room temperature, a solution of tert-butyl(dimethyl)silyl chloride (434 mg, 2.89 mmol) was added and the reaction was then stirred for an additional 1 h. The solvent was evaporated and residue was purified by flash chromatography (silica gel; 20% ethyl acetate/hexanes as eluant) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 5.03 (s, 2H), 4.05 (s, 3H), 0.95 (s, 9H), 0.19 (s, 6H). LC/MS: 480 (M+H+2).

Workup

  1. customThe solvent was evaporated
  2. customresidue was purified by flash chromatography (silica gel; 20% ethyl acetate/hexanes as eluant)

Sources & evidence

ORD record
ord-7ab34348ac11423d9ea8bc1e66d90448
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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